NZ268575A - N-[[1-[4-(4-fluorophenoxy)butyl]-4-piperidinyl]-n-methylamino] -2-benzothiazol-5(or 6)-ol; pharmaceutical compositions - Google Patents

N-[[1-[4-(4-fluorophenoxy)butyl]-4-piperidinyl]-n-methylamino] -2-benzothiazol-5(or 6)-ol; pharmaceutical compositions

Info

Publication number: NZ268575A
Authority: NZ; New Zealand
Prior art keywords: compound; grams; solution; piperidinyl; pct
Prior art date: 1993-06-11

Application number

NZ268575A

Other languages

English (en)

Inventor

Jozef Jan Pieter Heykants

Marcel Jan Maria Borgers

Doris Wilhelm

Original Assignee

Janssen Pharmaceutica Nv

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1993-06-11

Filing date

1994-06-06

Publication date

1996-08-27

1994-06-06 Application filed by Janssen Pharmaceutica Nv filed Critical Janssen Pharmaceutica Nv

1996-08-27 Publication of NZ268575A publication Critical patent/NZ268575A/en

Links

125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 title claims abstract description 15
239000008194 pharmaceutical composition Substances 0.000 title abstract description 5
150000001875 compounds Chemical class 0.000 claims abstract description 54
150000003839 salts Chemical class 0.000 claims abstract description 19
239000002253 acid Substances 0.000 claims abstract description 15
125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 claims abstract description 9
239000001257 hydrogen Substances 0.000 claims abstract description 4
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 4
125000004435 hydrogen atom Chemical class [H]* 0.000 claims abstract description 4
239000000243 solution Substances 0.000 claims description 32
239000000203 mixture Substances 0.000 claims description 27
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 12
VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 claims description 11
239000003814 drug Substances 0.000 claims description 9
239000004480 active ingredient Substances 0.000 claims description 7
239000003416 antiarrhythmic agent Substances 0.000 claims description 6
239000002202 Polyethylene glycol Substances 0.000 claims description 5
238000001816 cooling Methods 0.000 claims description 5
238000000034 method Methods 0.000 claims description 5
229920001223 polyethylene glycol Polymers 0.000 claims description 5
FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric Acid Chemical compound [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 claims description 4
JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 claims description 4
LXCFILQKKLGQFO-UHFFFAOYSA-N methylparaben Chemical compound COC(=O)C1=CC=C(O)C=C1 LXCFILQKKLGQFO-UHFFFAOYSA-N 0.000 claims description 4
230000008569 process Effects 0.000 claims description 3
238000003756 stirring Methods 0.000 claims description 3
239000003513 alkali Substances 0.000 claims description 2
230000003288 anthiarrhythmic effect Effects 0.000 claims description 2
238000009835 boiling Methods 0.000 claims description 2
239000003153 chemical reaction reagent Substances 0.000 claims description 2
239000012458 free base Substances 0.000 claims description 2
229940102223 injectable solution Drugs 0.000 claims description 2
238000002347 injection Methods 0.000 claims description 2
239000007924 injection Substances 0.000 claims description 2
235000014655 lactic acid Nutrition 0.000 claims description 2
235000010270 methyl p-hydroxybenzoate Nutrition 0.000 claims description 2
231100000252 nontoxic Toxicity 0.000 claims description 2
230000003000 nontoxic effect Effects 0.000 claims description 2
235000010232 propyl p-hydroxybenzoate Nutrition 0.000 claims description 2
QELSKZZBTMNZEB-UHFFFAOYSA-N propylparaben Chemical compound CCCOC(=O)C1=CC=C(O)C=C1 QELSKZZBTMNZEB-UHFFFAOYSA-N 0.000 claims description 2
229960003415 propylparaben Drugs 0.000 claims description 2
WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 claims 3
DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 claims 3
125000002887 hydroxy group Chemical group [H]O* 0.000 claims 2
239000000829 suppository Substances 0.000 claims 2
244000264242 Descurainia sophia Species 0.000 claims 1
229960004217 benzyl alcohol Drugs 0.000 claims 1
235000019445 benzyl alcohol Nutrition 0.000 claims 1
238000001914 filtration Methods 0.000 claims 1
239000004310 lactic acid Substances 0.000 claims 1
238000002156 mixing Methods 0.000 claims 1
239000008159 sesame oil Substances 0.000 claims 1
235000011803 sesame oil Nutrition 0.000 claims 1
239000004094 surface-active agent Substances 0.000 claims 1
150000003626 triacylglycerols Chemical class 0.000 claims 1
239000008215 water for injection Substances 0.000 claims 1
206010003119 arrhythmia Diseases 0.000 description 27
230000006793 arrhythmia Effects 0.000 description 24
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 18
238000002360 preparation method Methods 0.000 description 10
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
239000003826 tablet Substances 0.000 description 8
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 7
238000012360 testing method Methods 0.000 description 7
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 6
230000036982 action potential Effects 0.000 description 6
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241000282472 Canis lupus familiaris Species 0.000 description 4
PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 4
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
230000002159 abnormal effect Effects 0.000 description 4
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239000000725 suspension Substances 0.000 description 4
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
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150000007513 acids Chemical class 0.000 description 3
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210000002837 heart atrium Anatomy 0.000 description 3
239000007788 liquid Substances 0.000 description 3
HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 3
VNWKTOKETHGBQD-UHFFFAOYSA-N methane Natural products C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 3
239000011541 reaction mixture Substances 0.000 description 3
239000000741 silica gel Substances 0.000 description 3
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210000001013 sinoatrial node Anatomy 0.000 description 3
229910000029 sodium carbonate Inorganic materials 0.000 description 3
239000007787 solid Substances 0.000 description 3
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WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 2
206010061216 Infarction Diseases 0.000 description 2
GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 2
FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 2
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
DBMJMQXJHONAFJ-UHFFFAOYSA-M Sodium laurylsulphate Chemical compound [Na+].CCCCCCCCCCCCOS([O-])(=O)=O DBMJMQXJHONAFJ-UHFFFAOYSA-M 0.000 description 2
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
208000001871 Tachycardia Diseases 0.000 description 2
206010047281 Ventricular arrhythmia Diseases 0.000 description 2
239000000654 additive Substances 0.000 description 2
WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 description 2
239000008280 blood Substances 0.000 description 2
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230000037396 body weight Effects 0.000 description 2
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210000004027 cell Anatomy 0.000 description 2
239000011248 coating agent Substances 0.000 description 2
238000000576 coating method Methods 0.000 description 2
230000003292 diminished effect Effects 0.000 description 2
230000002526 effect on cardiovascular system Effects 0.000 description 2
239000000284 extract Substances 0.000 description 2
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235000011187 glycerol Nutrition 0.000 description 2
230000007574 infarction Effects 0.000 description 2
239000004615 ingredient Substances 0.000 description 2
208000028867 ischemia Diseases 0.000 description 2
239000008101 lactose Substances 0.000 description 2
230000003859 lipid peroxidation Effects 0.000 description 2
239000003921 oil Substances 0.000 description 2
235000019198 oils Nutrition 0.000 description 2
239000002674 ointment Substances 0.000 description 2
229940100688 oral solution Drugs 0.000 description 2
239000012044 organic layer Substances 0.000 description 2
230000000144 pharmacologic effect Effects 0.000 description 2
239000006187 pill Substances 0.000 description 2
BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
239000001267 polyvinylpyrrolidone Substances 0.000 description 2
229920000036 polyvinylpyrrolidone Polymers 0.000 description 2
235000013855 polyvinylpyrrolidone Nutrition 0.000 description 2
239000008213 purified water Substances 0.000 description 2
230000002336 repolarization Effects 0.000 description 2
230000004043 responsiveness Effects 0.000 description 2
239000011780 sodium chloride Substances 0.000 description 2
235000019333 sodium laurylsulphate Nutrition 0.000 description 2
ILJOYZVVZZFIKA-UHFFFAOYSA-M sodium;1,1-dioxo-1,2-benzothiazol-3-olate;hydrate Chemical compound O.[Na+].C1=CC=C2C(=O)[N-]S(=O)(=O)C2=C1 ILJOYZVVZZFIKA-UHFFFAOYSA-M 0.000 description 2
239000002904 solvent Substances 0.000 description 2
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230000000638 stimulation Effects 0.000 description 2
230000002459 sustained effect Effects 0.000 description 2
230000006794 tachycardia Effects 0.000 description 2
208000003663 ventricular fibrillation Diseases 0.000 description 2
206010047302 ventricular tachycardia Diseases 0.000 description 2
ORIIXCOYEOIFSN-UHFFFAOYSA-N 1,3-benzothiazol-6-ol Chemical compound OC1=CC=C2N=CSC2=C1 ORIIXCOYEOIFSN-UHFFFAOYSA-N 0.000 description 1
ISASIXVNMVNAPN-UHFFFAOYSA-N 2-[methyl(piperidin-4-yl)amino]-1,3-benzothiazol-5-ol Chemical compound N=1C2=CC(O)=CC=C2SC=1N(C)C1CCNCC1 ISASIXVNMVNAPN-UHFFFAOYSA-N 0.000 description 1
JIGMMESOZQATDW-UHFFFAOYSA-N 2-[methyl(piperidin-4-yl)amino]-1,3-benzothiazol-6-ol;dihydrobromide Chemical compound Br.Br.N=1C2=CC=C(O)C=C2SC=1N(C)C1CCNCC1 JIGMMESOZQATDW-UHFFFAOYSA-N 0.000 description 1
239000005995 Aluminium silicate Substances 0.000 description 1
206010002091 Anaesthesia Diseases 0.000 description 1
COVZYZSDYWQREU-UHFFFAOYSA-N Busulfan Chemical compound CS(=O)(=O)OCCCCOS(C)(=O)=O COVZYZSDYWQREU-UHFFFAOYSA-N 0.000 description 1
241000700198 Cavia Species 0.000 description 1
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 1
FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 1
239000001856 Ethyl cellulose Substances 0.000 description 1
ZZSNKZQZMQGXPY-UHFFFAOYSA-N Ethyl cellulose Chemical compound CCOCC1OC(OC)C(OCC)C(OCC)C1OC1C(O)C(O)C(OC)C(CO)O1 ZZSNKZQZMQGXPY-UHFFFAOYSA-N 0.000 description 1
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208000010496 Heart Arrest Diseases 0.000 description 1
241001465754 Metazoa Species 0.000 description 1
229920000168 Microcrystalline cellulose Polymers 0.000 description 1
GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
102000004257 Potassium Channel Human genes 0.000 description 1
208000000418 Premature Cardiac Complexes Diseases 0.000 description 1
206010063837 Reperfusion injury Diseases 0.000 description 1
240000007651 Rubus glaucus Species 0.000 description 1
235000011034 Rubus glaucus Nutrition 0.000 description 1
235000009122 Rubus idaeus Nutrition 0.000 description 1
229910021607 Silver chloride Inorganic materials 0.000 description 1
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150000001298 alcohols Chemical class 0.000 description 1
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238000001949 anaesthesia Methods 0.000 description 1
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230000000141 anti-hypoxic effect Effects 0.000 description 1
230000003126 arrythmogenic effect Effects 0.000 description 1
210000001367 artery Anatomy 0.000 description 1
239000002585 base Substances 0.000 description 1
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239000011230 binding agent Substances 0.000 description 1
239000012472 biological sample Substances 0.000 description 1
230000036471 bradycardia Effects 0.000 description 1
208000006218 bradycardia Diseases 0.000 description 1
230000001964 calcium overload Effects 0.000 description 1
229940097217 cardiac glycoside Drugs 0.000 description 1
239000002368 cardiac glycoside Substances 0.000 description 1
238000013194 cardioversion Methods 0.000 description 1
239000000969 carrier Substances 0.000 description 1
125000001309 chloro group Chemical group Cl* 0.000 description 1
229960001701 chloroform Drugs 0.000 description 1
230000001684 chronic effect Effects 0.000 description 1
KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 1
229940082627 class iii antiarrhythmics Drugs 0.000 description 1
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229940125782 compound 2 Drugs 0.000 description 1
208000029078 coronary artery disease Diseases 0.000 description 1
239000006071 cream Substances 0.000 description 1
HCAJEUSONLESMK-UHFFFAOYSA-N cyclohexylsulfamic acid Chemical compound OS(=O)(=O)NC1CCCCC1 HCAJEUSONLESMK-UHFFFAOYSA-N 0.000 description 1
230000006378 damage Effects 0.000 description 1
230000002939 deleterious effect Effects 0.000 description 1
239000003937 drug carrier Substances 0.000 description 1
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238000011067 equilibration Methods 0.000 description 1
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239000000796 flavoring agent Substances 0.000 description 1
235000019634 flavors Nutrition 0.000 description 1
239000007903 gelatin capsule Substances 0.000 description 1
239000011521 glass Substances 0.000 description 1
150000002334 glycols Chemical class 0.000 description 1
125000005843 halogen group Chemical group 0.000 description 1
150000004677 hydrates Chemical class 0.000 description 1
239000008172 hydrogenated vegetable oil Substances 0.000 description 1
125000004356 hydroxy functional group Chemical group O* 0.000 description 1
239000005457 ice water Substances 0.000 description 1
238000000338 in vitro Methods 0.000 description 1
238000001727 in vivo Methods 0.000 description 1
230000002401 inhibitory effect Effects 0.000 description 1
230000035987 intoxication Effects 0.000 description 1
231100000566 intoxication Toxicity 0.000 description 1
238000011835 investigation Methods 0.000 description 1
230000000302 ischemic effect Effects 0.000 description 1
NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 1
210000005240 left ventricle Anatomy 0.000 description 1
231100000518 lethal Toxicity 0.000 description 1
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239000000314 lubricant Substances 0.000 description 1
235000019359 magnesium stearate Nutrition 0.000 description 1
229910052943 magnesium sulfate Inorganic materials 0.000 description 1
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239000001923 methylcellulose Substances 0.000 description 1
235000010981 methylcellulose Nutrition 0.000 description 1
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235000019813 microcrystalline cellulose Nutrition 0.000 description 1
239000008108 microcrystalline cellulose Substances 0.000 description 1
150000007522 mineralic acids Chemical class 0.000 description 1
150000004682 monohydrates Chemical class 0.000 description 1
210000003205 muscle Anatomy 0.000 description 1
208000010125 myocardial infarction Diseases 0.000 description 1
208000031225 myocardial ischemia Diseases 0.000 description 1
210000004165 myocardium Anatomy 0.000 description 1
229910017604 nitric acid Inorganic materials 0.000 description 1
239000006186 oral dosage form Substances 0.000 description 1
229940098462 oral drops Drugs 0.000 description 1
210000000056 organ Anatomy 0.000 description 1
150000007524 organic acids Chemical class 0.000 description 1
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LPMXVESGRSUGHW-HBYQJFLCSA-N ouabain Chemical compound O[C@@H]1[C@H](O)[C@@H](O)[C@H](C)O[C@H]1O[C@@H]1C[C@@]2(O)CC[C@H]3[C@@]4(O)CC[C@H](C=5COC(=O)C=5)[C@@]4(C)C[C@@H](O)[C@@H]3[C@@]2(CO)[C@H](O)C1 LPMXVESGRSUGHW-HBYQJFLCSA-N 0.000 description 1
210000003540 papillary muscle Anatomy 0.000 description 1
239000006072 paste Substances 0.000 description 1
239000003961 penetration enhancing agent Substances 0.000 description 1
230000010412 perfusion Effects 0.000 description 1
125000003386 piperidinyl group Chemical group 0.000 description 1
229910052697 platinum Inorganic materials 0.000 description 1
108020001213 potassium channel Proteins 0.000 description 1
230000003389 potentiating effect Effects 0.000 description 1
239000002244 precipitate Substances 0.000 description 1
230000002028 premature Effects 0.000 description 1
230000002265 prevention Effects 0.000 description 1
125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
230000000644 propagated effect Effects 0.000 description 1
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239000003642 reactive oxygen metabolite Substances 0.000 description 1
230000001105 regulatory effect Effects 0.000 description 1
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229910052709 silver Inorganic materials 0.000 description 1
239000004332 silver Substances 0.000 description 1
HKZLPVFGJNLROG-UHFFFAOYSA-M silver monochloride Chemical compound [Cl-].[Ag+] HKZLPVFGJNLROG-UHFFFAOYSA-M 0.000 description 1
229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
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Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/06—Antiarrhythmics

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
General Health & Medical Sciences (AREA)
Cardiology (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Bioinformatics & Cheminformatics (AREA)
Pharmacology & Pharmacy (AREA)
Engineering & Computer Science (AREA)
Animal Behavior & Ethology (AREA)
Heart & Thoracic Surgery (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Other In-Based Heterocyclic Compounds (AREA)
Hydrogenated Pyridines (AREA)
Compositions Of Macromolecular Compounds (AREA)
Thiazole And Isothizaole Compounds (AREA)
Silver Salt Photography Or Processing Solution Therefor (AREA)
Plural Heterocyclic Compounds (AREA)
Nitrogen- Or Sulfur-Containing Heterocyclic Ring Compounds With Rings Of Six Or More Members (AREA)

NZ268575A 1993-06-11 1994-06-06 N-[[1-[4-(4-fluorophenoxy)butyl]-4-piperidinyl]-n-methylamino] -2-benzothiazol-5(or 6)-ol; pharmaceutical compositions NZ268575A (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
EP93201685		1993-06-11

Publications (1)

Publication Number	Publication Date
NZ268575A true NZ268575A (en)	1996-08-27

Family

ID=8213890

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NZ268575A NZ268575A (en)	1993-06-11	1994-06-06	N-[[1-[4-(4-fluorophenoxy)butyl]-4-piperidinyl]-n-methylamino] -2-benzothiazol-5(or 6)-ol; pharmaceutical compositions

Country Status (34)

Country	Link
US (1)	US5691354A (ru)
EP (1)	EP0701556B1 (ru)
JP (1)	JP3498145B2 (ru)
KR (1)	KR100337984B1 (ru)
CN (1)	CN1039120C (ru)
AT (1)	ATE159254T1 (ru)
AU (1)	AU678841B2 (ru)
BG (1)	BG62968B1 (ru)
BR (1)	BR9406765A (ru)
CA (1)	CA2163018A1 (ru)
CZ (1)	CZ285766B6 (ru)
DE (1)	DE69406284T2 (ru)
DK (1)	DK0701556T3 (ru)
ES (1)	ES2108471T3 (ru)
FI (1)	FI955916A (ru)
GR (1)	GR3025805T3 (ru)
HU (1)	HU221620B1 (ru)
IL (1)	IL109975A (ru)
LV (1)	LV11544B (ru)
MY (1)	MY111222A (ru)
NO (1)	NO305123B1 (ru)
NZ (1)	NZ268575A (ru)
OA (1)	OA10201A (ru)
PH (1)	PH31126A (ru)
PL (1)	PL176775B1 (ru)
RO (1)	RO115523B1 (ru)
RU (1)	RU2122546C1 (ru)
SG (1)	SG48821A1 (ru)
SI (1)	SI9420036A (ru)
SK (1)	SK281175B6 (ru)
TW (1)	TW282469B (ru)
UA (1)	UA41936C2 (ru)
WO (1)	WO1994029305A1 (ru)
ZA (1)	ZA944106B (ru)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
IL150650A0 (en)	2000-01-20	2003-02-12	Eisai Co Ltd	Piperidine derivatives and pharmaceutical compositions containing the same

Family Cites Families (6)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4861785A (en) *	1984-12-03	1989-08-29	Janssen Pharmaceutica N.V.	Benzoxazol-and benzothiazolamine derivatives, useful as anti-anoxic agents
CA1260474A (en) *	1984-12-03	1989-09-26	Raymond A. Stokbroekx	Benzoxazol- and benzothiazolamine derivatives
US5010198A (en) *	1984-12-03	1991-04-23	Janssen Pharmaceutica N.V.	Intermediates for the synthesis of benzoxazol- and benzothiazolamine derivatives, useful as anti-anoxic agents
KR930005004B1 (ko) *	1985-04-15	1993-06-11	쟈안센 파아마슈우티카 엔. 부이.	치환된 n-[(4-피페리디닐)알킬]이환 축합 옥사졸아민 및 티아졸아민의 제조방법
US4749702A (en) *	1985-04-15	1988-06-07	Janssen Pharmaceutica N. V.	Antidepressive substituted N-[(4-piperidinyl)alkyl] bicyclic condensed oxazol- and thiazolamines
ZW1992A1 (en) *	1991-02-25	1993-09-22	Janssen Pharmaceutica Nv	4-/(2-benzotiazolyl)methylamino/-b-/(3,4-difluorephenoxy)methyl/-1-piperidine ethanol

1994
- 1994-05-30 TW TW083104888A patent/TW282469B/zh active
- 1994-06-06 SG SG1996002091A patent/SG48821A1/en unknown
- 1994-06-06 RU RU96100754A patent/RU2122546C1/ru not_active IP Right Cessation
- 1994-06-06 EP EP94920909A patent/EP0701556B1/en not_active Expired - Lifetime
- 1994-06-06 PL PL94311965A patent/PL176775B1/pl not_active IP Right Cessation
- 1994-06-06 ES ES94920909T patent/ES2108471T3/es not_active Expired - Lifetime
- 1994-06-06 US US08/549,830 patent/US5691354A/en not_active Expired - Fee Related
- 1994-06-06 AT AT94920909T patent/ATE159254T1/de not_active IP Right Cessation
- 1994-06-06 CA CA002163018A patent/CA2163018A1/en not_active Abandoned
- 1994-06-06 UA UA95125445A patent/UA41936C2/ru unknown
- 1994-06-06 DE DE69406284T patent/DE69406284T2/de not_active Expired - Fee Related
- 1994-06-06 CN CN94192409A patent/CN1039120C/zh not_active Expired - Fee Related
- 1994-06-06 AU AU71838/94A patent/AU678841B2/en not_active Ceased
- 1994-06-06 WO PCT/EP1994/001849 patent/WO1994029305A1/en active IP Right Grant
- 1994-06-06 RO RO95-02140A patent/RO115523B1/ro unknown
- 1994-06-06 BR BR9406765A patent/BR9406765A/pt not_active Application Discontinuation
- 1994-06-06 KR KR1019950705179A patent/KR100337984B1/ko not_active IP Right Cessation
- 1994-06-06 CZ CZ953192A patent/CZ285766B6/cs not_active IP Right Cessation
- 1994-06-06 NZ NZ268575A patent/NZ268575A/en unknown
- 1994-06-06 DK DK94920909.2T patent/DK0701556T3/da active
- 1994-06-06 JP JP50131495A patent/JP3498145B2/ja not_active Expired - Fee Related
- 1994-06-06 SI SI9420036A patent/SI9420036A/sl not_active IP Right Cessation
- 1994-06-06 HU HU9501971A patent/HU221620B1/hu not_active IP Right Cessation
- 1994-06-06 SK SK1544-95A patent/SK281175B6/sk unknown
- 1994-06-10 PH PH48422A patent/PH31126A/en unknown
- 1994-06-10 IL IL10997594A patent/IL109975A/xx not_active IP Right Cessation
- 1994-06-10 MY MYPI94001484A patent/MY111222A/en unknown
- 1994-06-10 ZA ZA944106A patent/ZA944106B/xx unknown
1995
- 1995-11-27 NO NO954801A patent/NO305123B1/no unknown
- 1995-12-08 FI FI955916A patent/FI955916A/fi not_active IP Right Cessation
- 1995-12-08 BG BG100210A patent/BG62968B1/bg unknown
- 1995-12-11 OA OA60754A patent/OA10201A/en unknown
1996
- 1996-01-11 LV LVP-96-06A patent/LV11544B/en unknown
1997
- 1997-12-30 GR GR970403451T patent/GR3025805T3/el unknown

Also Published As

Publication number	Publication date
SK281175B6 (sk)	2000-12-11
JP3498145B2 (ja)	2004-02-16
NO954801L (no)	1995-11-27
PL311965A1 (en)	1996-03-18
MY111222A (en)	1999-09-30
BG62968B1 (bg)	2000-12-29
ATE159254T1 (de)	1997-11-15
NO954801D0 (no)	1995-11-27
FI955916A0 (fi)	1995-12-08
IL109975A0 (en)	1994-10-07
PL176775B1 (pl)	1999-07-30
CN1039120C (zh)	1998-07-15
TW282469B (ru)	1996-08-01
CZ285766B6 (cs)	1999-11-17
IL109975A (en)	1999-04-11
AU678841B2 (en)	1997-06-12
EP0701556A1 (en)	1996-03-20
SI9420036A (en)	1996-10-31
CN1125443A (zh)	1996-06-26
LV11544B (en)	1997-08-20
HUT73679A (en)	1996-09-30
FI955916A (fi)	1995-12-08
DK0701556T3 (da)	1998-01-26
HU9501971D0 (en)	1995-09-28
AU7183894A (en)	1995-01-03
DE69406284T2 (de)	1998-02-19
EP0701556B1 (en)	1997-10-15
SK154495A3 (en)	1996-06-05
RO115523B1 (ro)	2000-03-30
OA10201A (en)	1996-12-18
NO305123B1 (no)	1999-04-06
GR3025805T3 (en)	1998-03-31
DE69406284D1 (de)	1997-11-20
RU2122546C1 (ru)	1998-11-27
KR100337984B1 (ko)	2002-10-25
UA41936C2 (ru)	2001-10-15
BG100210A (bg)	1996-07-31
ZA944106B (en)	1995-12-11
LV11544A (lv)	1996-10-20
BR9406765A (pt)	1996-02-21
WO1994029305A1 (en)	1994-12-22
PH31126A (en)	1998-02-23
JPH08511014A (ja)	1996-11-19
HU221620B1 (hu)	2002-12-28
CA2163018A1 (en)	1994-12-22
CZ319295A3 (en)	1996-03-13
ES2108471T3 (es)	1997-12-16
SG48821A1 (en)	1998-05-18
US5691354A (en)	1997-11-25

Legal Events

Date	Code	Title	Description
2001-06-29	RENW	Renewal (renewal fees accepted)
2004-06-25	RENW	Renewal (renewal fees accepted)

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